OK, so maybe I am missing something here: you can only put earned income into an IRA or 401k, right? So where is the earned income from if you are doing your rollovers in retirement?
One thing to understand, I am 55 and at least 10 years from retirement. Which changes things a lot: I have only 5 years of retirement before I need to make 401k withdrawals, and 7 years of retirement before I take Social Security.
You've got a couple of things off here, and if you can wrap your head around them, and plan accordingly, we're talking well over 6 figures to your bottom line.
- You should (pretty much always) never roll over a 401(k) to Roth in a high tax bracket. Broad rule of thumb for this is that 15% bracket is OK, above is not, with the caveat being that you have some major taxable events in the future, such as a very large taxable income in retirement. (IE don't roll over your 401k)
- The time to do Roth Conversions is when income is lowest, ide zero. While you do need income to 'Contribute' to an IRA or 401(k) you do not need income to Roll over. Therefore, if you retire, and your salary is removed, this is the time to roll over. I illustrate the income gap in this post: http://saverocity.com/finance/should-you-have-a-roth-401k-or-traditional-401k/
- The perfect financial solution will see you delaying 401(k) withdrawals as long as possible. For you, this is 15-16 years away, not 10. At this point, you will be faced with Required Minimum Distributions. Money that you've managed to roll over to Roth before that deadline is excluded from RMD.
- Social Security planning is it's own topic, but generally speaking, you would do best to take Social Security no sooner than Full Retirement Age (67, not 62) and if you can afford to wait longer, 70 is even better. This assumes that you do not die prematurely. The only reason to take at 62 is poverty, ill health, or an expectation that you will not live much longer, which for some, sadly is the case.
The 'perfect' plan will be to get to a financial position where you can retire and have some sort of income gap, EG if you can retire at 62, but not take Social Security or 401(k) money, living on taxable savings instead. Using these years of income gap to roll over into Roths an amount of money from the 401(k). This ensures that the Roth funds go to the back of the line (an account of last resort) and grow tax free, potentially forever.
This does depend on your own financial situation, IE if you have a modest amount in the 401(k) then you can do partial rollovers in a year or two, or maybe you don't even need to, because the RMD is so low that it doesn't make big impact.
However, you should also be contributing at least $24,000 to your work based 401(k), along with another $X from your reselling 401(k) so in the next 5-7 years contributions alone should exceed $100K, probably closer to $150K. If you can't do that, look at debt management and expenses to see if anything can be done.
You'd also benefit from doing back door Roths on top of this for another $6500 per year into the Roth.